Holiday rentals in Kailua
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Top-rated holiday rentals in Kailua
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Kailua Beach Park - 1 BR Cottage
Kailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!
Absolutely Oceanfront-60'Waterfall Pool-Legal
Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060
Beachfront Getaway - Hawaiian Princess Condo
Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.
Nai’a Suite at La Bella’s-Walk to Beach-Licensed
La Bella’s B&B is a High End Luxury home filled with charm and a touch of farmhouse/beach elegance. Two Suites are available for booking. Owners live onsite. Starbucks, Safeway, Gas Stations and Eateries are right across the street. Nai’a (Dolphin) Suite Offers: -Kitchenette -Private Bathroom -Separate Entrance -AC and Powerful high end fan -King size bed w/luxury bedding If you want a beautiful garden, great host family and a short walk to the beach this is the place for you.
♥ North Shore Paradise at Turtle Bay ♥
For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.
Studio- Ocean View Hideaway
Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.
Kailua Rental for Med/Long Term ($1,500/month)
Escape to beautiful Kailua and enjoy our cozy guest suite! Located in a quiet cul-de-sac, this unit provides modern amenities, a new full-sized bed and direct access to your own private lanai. Mountain views, nearby attractions, shopping, dining, and world-class beaches ensure an ideal destination for your next retreat! We welcome minimum stays of 30 days or more. Please contact for inquiry details. * 30 night minimum
Kailua Palm Studio. Walk to Beach! PERMITTED
Licensed, legal (NUC short term rental #1990/NUC-1819, Tax map key: 43073024) *not impacted by Honolulu ordinances banning short term **RECENTLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Kupono Services.
Lanikai Garden Studio - Licensed - Since 1985!
Neighboring construction discount 12/6 - 12/13 $225/night. Located just across the street from Beautiful Lanikai Beach, this home-within-a-room offers all the comforts of home in paradise! With ample space, windows, and tropical flora views, this home is a place where you can relax and unwind. With cool, quiet, and comfortable air-conditioning after a day at the beach! Licensed for short-term rentals since 1985!
Kailua Beach Cottage - 1990/NUC-1797
WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.
Oceanfront Studio - 100 Foot Wave Getaways
Open floor plan studio located on 2 beautiful acres fronting pristine beach. We offer a Privacy gate entrance for your security, parking on site within the gate.Steps to the sand and ocean. Minimal and beautiful Bali furnishings, full kitchen with all you need to prepare meals, luxurious soaking bathtub and hawaii style outdoor shower. Quiet,beautiful sunsets,stars at night.
Ocean Views 2 Bedroom - 100 Foot Wave Getaways
Welcome to the Ocean Views 2 Bedroom at 100 Foot Wave Getaways. Escape to your private beachfront suite, inspired by the legendary waves of Nazaré, and fall asleep to the sound of waves on the North Shore of Oahu with stunning ocean and mountain views and a luxurious king bed with organic Egyptian cotton sheets.
Popular amenities for Kailua holiday rentals
Stay near Kailua's top sights
Other great holiday rentals in Kailua
The Lebowski- Paradise Campervan
The Ohana Island Hut
Hibiscus Hale - Perfect for 2!
Peaceful cozy comfortable apartment
Best Kept Secret on Oahu! and WE ARE LICENSED!!!
Kaia Villa at Turtle Bay/North Shore Oahu
Honu Hideout at Turtle Bay
The Drifter - North Shore Loft - Relaxed Luxury
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $320 SGD | $321 SGD | $289 SGD | $289 SGD | $304 SGD | $304 SGD | $304 SGD | $295 SGD | $275 SGD | $294 SGD | $288 SGD | $297 SGD |
| Avg. temp | 22°C | 22°C | 23°C | 24°C | 24°C | 26°C | 26°C | 27°C | 26°C | 26°C | 24°C | 23°C |
Frequently Asked Questions
What are the best places to stay in Kailua?
Stays in central Kailua let you explore vibrant shops and restaurants, while accommodations near Lanikai offer relaxed beach access. Both areas are frequently suggested for those looking for a local experience.
What are the best things to do in Kailua with kids?
Kailua Beach Park has gentle waves for swimming, and the Kalapawai Market is known for casual snacks and treats. Kayaking on the bay and exploring nearby nature trails are also frequently suggested for families.
What are some of the best things to do in Kailua?
Explore kayaking or paddleboarding in the calm bay, hike up to the Lanikai Pillboxes, and unwind at Kailua Beach Park. Kailua’s farmers' markets, local eateries, and bike paths are also frequently suggested.
How is the weather in Kailua?
Kailua has warm temperatures throughout the year, ranging from about 65–85°F (18–30°C). Rain is more frequent in winter and early spring, while summers are sunnier with less rainfall.
When is the best time to visit Kailua?
May through September has warmer temperatures around 70–85°F (21–30°C) and less rainfall, making it a popular time for beach outings. Late spring and early fall are often enjoyed for smaller crowds and local festivals.
What are the best places to visit in Kailua?
Frequently suggested spots in Kailua include the white sands of Kailua Beach Park, the scenic Lanikai Beach, and the Pillbox Hike for panoramic coastal views. The neighborhood also has inviting local markets and art galleries.
What are some hiking trails in Kailua?
The Lanikai Pillbox Hike is frequently suggested for its scenic coastal views and moderate climb. Locals also explore forested paths in nearby natural reserves, where you can experience native plants and ocean breezes.
What are some family activities we can do in Kailua?
Families can explore calm swimming beaches, rent bikes for easy paths, or visit local playgrounds in Kailua. Kayaking, visiting markets, or observing wildlife at Kawainui Marsh are also popular choices among visitors with children.
What are some of the best day trip ideas from Kailua?
Day trips around Kailua can include exploring lush botanical gardens, visiting the North Shore’s surf spots, or hiking in forested preserves. The area also has popular historic sites and cultural centers within easy reach.
Are there any pet friendly accommodations available in Kailua?
Many accommodations in Kailua are pet friendly, especially around central neighborhoods and residential areas. Parks and outdoor cafes make it convenient for guests traveling with pets.
What are some local tips for visiting Kailua?
Weekdays generally feel quieter at popular beaches, and early mornings are good for catching sunrise views from Lanikai. Remember to respect local customs, pack out what you bring, and use reef-safe sunscreen to protect marine life.
What is Kailua known for?
Kailua is known for its wide, sandy beaches, calm turquoise waters, and relaxed community vibe. The area has scenic hiking, local food spots, and opportunities to experience traditional Hawaiian culture.
What are the best hidden gems to explore in Kailua?
Kailua has quiet local beaches, shaded marsh trails for birdwatching, and small independent shops where you can explore local crafts. Consider wandering untouristed sections of Kailua Beach or the nearby Kawainui Marsh trail for a more laid-back experience.
What are the best foods to try in Kailua?
Kailua has fresh poke bowls, local plate lunches, and tropical fruit smoothies that are often recommended. Shave ice and pastries from neighborhood bakeries add to the area’s favorite flavors.
What should I bring for a trip to Kailua?
Pack light, breathable clothing, swimwear, reef-safe sunscreen, and a sun hat for comfort in Kailua's warm weather. If you plan to hike or explore nature, closed-toe shoes and a reusable water bottle are often recommended.
What is the nightlife in Kailua like?
Kailua has a relaxed nightlife scene with welcoming bars, laid-back dining spots, and venues that occasionally feature live music. Most nightlife is concentrated in town, and evenings often center around enjoying local flavors in a casual atmosphere.
What are the most popular events or festivals in Kailua?
Kailua frequently hosts street fairs, annual parade celebrations around holidays, and open-air art markets. Late spring and holiday weekends are often filled with local music, food, and craft events.
Are there family friendly vacation rentals in Kailua?
Kailua has many family-friendly rentals, often located near beaches or local parks. These options typically include amenities like kitchens, outdoor space, and easy access to nearby attractions.
Quick stats about holiday rentals in Kailua
Total holiday rentals
Explore 340 holiday rentals in Kailua
Nightly prices starting at
Kailua holiday rentals start at $51 SGD per night before taxes and fees
Verified guest reviews
Over 10,940 verified reviews to help you choose
Family-friendly holiday rentals
200 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 40 rentals that welcome pets
Holiday rentals with a pool
90 properties feature pools
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Wifi availability
340 of Kailua holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Beachfront and Gym across Kailua rentals
4.8 Average rating
Kailua stays are highly rated by guests – averaging 4.8 out of 5!
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- Kailua Beach
- Kualoa Ranch
- Waimea Bay Beach
- Lanikai Beach
- Kepuhi Beach
- Ala Moana Beach Park
- Honolulu Zoo
- Banzai Pipeline
- Mālaekahana Beach
- Kapiolani Park Beach
- Kalama Beach
- Mākua Beach
- White Plains Beach
- Hanauma Bay
- Sans Souci Beach
- Nimitz Beach
- Waimea Bay Beach
- Ke Iki Beach
- Bishop Museum
- Kahala Hilton Beach
- Wet 'n' Wild Hawaii
- Waimea Valley
- Diamond Head Beach Park
- Kalani Beach
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